#1227 new
Brian Jones

SMTP timeouts

Reported by Brian Jones | August 4th, 2015 @ 04:50 AM

I have started having problems sending emails. I have several different accounts: 1 iCloud, 1 FastMail, and 2 Google Apps.

I have just moved to Berlin and into a new apartment, so it is possible this is a local network issue, but it is a broadband connection, I have restarted the router a couple of times, and the problem is not constant. I have never seen this problem anywhere else in my several years using the app, either, despite lots of travel and connections to far slower internet service.

I have had trouble sending to the FastMail account from the beginning. Then the Gmail accounts stopped working. Now I wake up this morning and the iCloud account that has been working for several days has also stopped working.

The error message I get follows this pattern (this one is for iCloud):

04:41:52 Sending request (30)
04:41:52 Handling request
04:41:52 Clearing connection to smtp.mail.me.com
04:41:52 Ready to run action
04:41:52 Clearing connection to smtp.mail.me.com
04:41:52 Trying to connect to smtp.mail.me.com on port 587
04:43:08 Waited 75 seconds on write.

04:43:08 Error: Failed connecting to host (smtp.mail.me.com:587).
“error:0200203C:system library:connect:Operation timed out” “error:2007306E:BIO routines:CONN_STATE:nbio connect error” 04:43:08 Error code: 2
04:43:08 Failed action (0). Reset observed read/write timeouts: 40/40

04:43:08 Handling reply

I have successfully sent emails from FastMail and Gmail by connecting to a VPN using TunnelBear. I don’t know why that worked (perhaps it was a simple coincidence of timing but it is the only time the FastMail account has worked).

I tried the TunnelBear approach again this morning to send with iCloud and that did not work.

Thanks for the help.

Comments and changes to this ticket

  • Brian Jones

    Brian Jones August 4th, 2015 @ 04:51 AM

    I forgot to mention: I am on OS X 10.10.4.

    This problem started with the most recent stable version of MailMate. I have switched to beta builds and am now running the most recent beta build and still see the problem.

  • benny

    benny August 5th, 2015 @ 06:00 PM

    Let's focus on 1 server. Try experimenting with connecting manually. Like this:

    openssl s_client -connect smtp.mail.me.com:587 -starttls smtp -crlf

    Does that work?

    IMAP works?

    Try updating to the latest beta in the Software Update preferences pane.

  • Mason Phillips

    Mason Phillips August 11th, 2015 @ 09:13 PM

    I'm experiencing the same general thing with SMTP issues (receiving is working fine).

    phillipsmn$ openssl s_client -connect njmm-mc2k.accessdomain.com:465 -starttls smtp
    connect: Operation timed out
    connect:errno=60

    phillipsmn$ openssl s_client -connect njmm-mc2k.accessdomain.com:587 -starttls smtp
    connect: Operation timed out
    connect:errno=60

    phillipsmn$ openssl s_client -connect njmm-mc2k.accessdomain.com:587 -starttls smtp -crlf
    connect: Operation timed out
    connect:errno=60

    It is only with this server, as iCloud mail and Gmail is working fine. But this is my work email so any insight would be greatly appreciated. If it will help, I've double-checked settings with our host and here's a link to their support page - https://mediatemple.net/community/products/dv/204405084/how-do-i-co...

  • Brian Jones

    Brian Jones August 12th, 2015 @ 03:50 AM

    I'm sorry; I missed the notification with your initial help, Benny.

    The iCloud and Gmail problems were temporary and the FastMail problem was fixed by using a proxy server of theirs. So I had only posted here once FastMail had been joined by iCloud and Gmail and the problem had seemed to become general, but it turns out those were separate issues after all and the FastMail one was the only persistent one and wasn't to do with MailMate.

    No idea what the iCloud and Gmail stuff was about, but given that it was temporary it was probably some networking thing and nothing to do with MailMate either.

    Thanks for the help.

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Mac OS X email client.

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